CA2129528C - N-[(pyrimidin-2-yl)aminocarbonyl]-benzenesulfonamides herbicides - Google Patents

N-[(pyrimidin-2-yl)aminocarbonyl]-benzenesulfonamides herbicides Download PDF

Info

Publication number: CA2129528C
Authority: CA; Canada
Prior art keywords: methyl; formula; pyrimidin; fluorine; aminocarbonyl
Prior art date: 1992-02-28
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002129528A

Other languages

English (en)

Other versions

CA2129528A1 (fr

Inventor

Horst Mayer

Gerhard Hamprecht

Karl-Otto Westphalen

Matthias Gerber

Uwe Kardorff

Helmut Walter

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-02-28

Filing date

1993-02-16

Publication date

2005-11-22

1992-02-28 Priority claimed from DE4206145A external-priority patent/DE4206145A1/de

1993-02-16 Application filed by BASF SE filed Critical BASF SE

1993-09-02 Publication of CA2129528A1 publication Critical patent/CA2129528A1/fr

2005-11-22 Application granted granted Critical

2005-11-22 Publication of CA2129528C publication Critical patent/CA2129528C/fr

2013-02-16 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 title claims abstract description 15
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 title description 5
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 title description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 66
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 38
-1 methyl sulphonyl Chemical group 0.000 claims abstract description 36
239000011737 fluorine Substances 0.000 claims abstract description 24
229910052731 fluorine Inorganic materials 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
239000001257 hydrogen Substances 0.000 claims abstract description 23
150000003839 salts Chemical class 0.000 claims abstract description 19
UJJQRJPAQKUPAQ-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-pyrimidin-2-ylurea Chemical class C=1C=CC=CC=1S(=O)(=O)NC(=O)NC1=NC=CC=N1 UJJQRJPAQKUPAQ-UHFFFAOYSA-N 0.000 claims abstract description 17
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 17
238000000034 method Methods 0.000 claims abstract description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 14
239000000460 chlorine Chemical group 0.000 claims abstract description 7
239000004009 herbicide Substances 0.000 claims abstract description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
OJWYYSVOSNWCCE-UHFFFAOYSA-N 2-methoxyethyl hypofluorite Chemical group COCCOF OJWYYSVOSNWCCE-UHFFFAOYSA-N 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 30
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 19
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
229940124530 sulfonamide Drugs 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 11
150000003456 sulfonamides Chemical class 0.000 claims description 11
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 5
239000012948 isocyanate Substances 0.000 claims description 5
150000002513 isocyanates Chemical class 0.000 claims description 4
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims description 4
150000005006 2-aminopyrimidines Chemical class 0.000 claims description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 3
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
239000012050 conventional carrier Substances 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
230000008635 plant growth Effects 0.000 claims 1
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 1
125000001424 substituent group Chemical group 0.000 abstract description 3
125000000217 alkyl group Chemical group 0.000 abstract description 2
229910052736 halogen Inorganic materials 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract 1
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
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238000000926 separation method Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
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QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
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AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
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RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

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Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

CA002129528A 1992-02-28 1993-02-16 N-[(pyrimidin-2-yl)aminocarbonyl]-benzenesulfonamides herbicides Expired - Fee Related CA2129528C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE4206145A DE4206145A1 (de)	1992-02-28	1992-02-28	Herbizide n-((pyrimidin-2-yl)aminocarbonyl)benzolfulfonamide
DEP4206145.8		1992-02-28
PCT/EP1993/000362 WO1993016998A1 (fr)	1992-02-28	1993-02-16	N-[(pyrimidin-2-yl)aminocarbonyl] sulfamides benzeniques herbicides

Publications (2)

Publication Number	Publication Date
CA2129528A1 CA2129528A1 (fr)	1993-09-02
CA2129528C true CA2129528C (fr)	2005-11-22

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Application Number	Title	Priority Date	Filing Date
CA002129528A Expired - Fee Related CA2129528C (fr)	1992-02-28	1993-02-16	N-[(pyrimidin-2-yl)aminocarbonyl]-benzenesulfonamides herbicides

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CA (1)	CA2129528C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19544743A1 (de) *	1995-12-01	1997-06-05	Hoechst Schering Agrevo Gmbh	5-Acylamino-2-alkoxycarbonylphenylsulfonylharnstoffe als selektive Herbizide

1993
- 1993-02-16 CA CA002129528A patent/CA2129528C/fr not_active Expired - Fee Related

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CA2129528A1 (fr)	1993-09-02

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1999-10-06	EEER	Examination request
2012-02-16	MKLA	Lapsed

Publication	Publication Date	Title
CA2094917C (fr)	2002-12-31	N-[(1,3,5-triazin-2-yl)-aminocarbonyl]-benzenesulfonamides herbicides
JP2986910B2 (ja)	1999-12-06	除草剤および植物生長調整剤としてのピリジルスルホニル尿素、それらの製造方法およびそれらの用途
US5612286A (en)	1997-03-18	Herbicidal N-[pyrimidin-2-ly) aminocarbonyl]-benzenesulfonamides
JP2818799B2 (ja)	1998-10-30	複素環式置換基を有するスルホニル尿素、それらの製造方法および除草剤としてのそれらの用途
CA2011987C (fr)	1999-08-10	Esters herbicides de l'acide 1,3,5-triazin-2-ylaminocarbonyla-minosulfonylbenzoiques, leur preparation et leur utilisation
US5488029A (en)	1996-01-30	Herbicidal N- [1,3,5-riazin-2-yl)-aminocarbonyl]-benzenesulfonamides
EP0668858B1 (fr)	1997-01-08	Sulfonylurees a action herbicide, leur procede de fabrication et leur utilisation
US5434124A (en)	1995-07-18	Sulfonylurea derivatives and their use
US5591694A (en)	1997-01-07	Herbicidal sulfonylureas
CA2129528C (fr)	2005-11-22	N-[(pyrimidin-2-yl)aminocarbonyl]-benzenesulfonamides herbicides
AU644291B1 (en)	1993-12-02	Herbicidal N-{(1,3,5-triazin-2-yl)-aminocarbonyl}- benzenesulfonamides
IL102075A (en)	1996-10-16	N-[(1,3,5-triazin-2-YL)aminocarbonyl] benzenesulfonamides their manufacture and their use as herbicides
SK279182B6 (sk)	1998-07-08	N-[(1,3,5-triazín-2-yl)aminokarbonyl]benzénsulfóna